Anticholinergic agents. 2. Absolute configurations of 2-methyl-1,1-diphenyl-3-(1-piperidyl)-1-propanol and 2-methyl-1,1-diphenyl-3-(1-pyrrolidyl)-1-propanol. Crystal structures of the corresponding mandelates.
Racemic 2-methyl-1,1-diphenyl-3-(1-piperidyl)-1-propanol (4) and 2-methyl-1,1-diphenyl-3-(1-pyrrolidyl)-1-propanol (5) have been synthesized and optically resolved employing (R)- and (S)-mandelic acid, respectively, as resolving agents. The absolute configurations of the enantiomers of 4 and 5 have been established as (-)-(R) and (+)-(S) by crystal structure analyses of (-)-(R)-2-methyl-1,1-diphenyl-3-(1-piperidinio)-1-propanol (+)-(S)-mandelate and (+)-(S)-2-methyl-1,1-diphenyl-3-(1-pyrrolidinio)-1-propanol (-)-(R)-mandelate. The corresponding methiodides have been prepared.
Sjö
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Department of Pharmacy, University of Oslo, Norway.
Groth
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P
Aasen
A J
AJ
D003461:Crystallography; D008333:Mandelic Acids / Q000737:chemistry*; D008968:Molecular Conformation; D010276:Parasympatholytics / Q000138:chemical synthesis / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000494:pharmacology; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013237:Stereoisomerism
D008333:Mandelic Acids; D010276:Parasympatholytics; D010880:Piperidines; D011759:Pyrrolidines; C067454:2-methyl-1,1-diphenyl-3-(1-pyrrolidyl)-1-propanol; C067455:2-methyl-1,1-diphenyl-3-(1-piperidinyl)-1-propanol